Benzylamine derivative



-BENZYLAMINE DERIVATIVE Seymour L. Shapiro, Hastings on Hudson, and Louis 6 Freedman, Bronxville, N.Y., assiguors to U. S. Vitamin and Pharmaceutical Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application December 29, 1958 Serial No. 783,136

1 Claim. (Cl. 260-268) This invention is concerned with bis-N ,N -(N'-[N"- benzylcarbamido]methylcarbamido)piperazine of the following formula (k-NHCHa-(hJ-IIT-CHQ 0 which is an anti-inflammatory agent of high potency and as such has therapeutic utility.

Example 1 2,921,074 Patented Jan. 12, 1960 piperazine reactant which in turn is prepared according to the equation below H oonnomooont 1 a l 1+ 0oNoHT-c0oEt J I N N n doNnonzoooEt Piperazine (10.0 g.) was dissolved in 250 m1. of ethyl acetate and 13.0 g. of carbethoxymethyl isocyanate in 100 ml. of ethyl acetate added dropwise over 1 hour, with stirring. After storage at 20 C. for 24 hours, 10.75 g. of the bis-ester (I) was collected, M.P. 206-208 C.

The bis-ester (I), (4.0 g.) was dissolved in 25 ml. of methanol and treated with 5.0 g. of benzylamine. Upon storage at 20 C. for 10 days, a total of 4.32 g. (80%) of product, bis-N ,N -(N'-[N"-benzylcarbamido]methylcarbamido)piperazine, was obtained which when recrystallized (ethanol) melted at l97-203 C.

Analysis.Calcd. for C H N O C, 61.8; H, 6.5. Found: C, 61.2; H, 6.6.

The product has a minimum lethal dose of 200 mg./kg. in mice (subcutaneous) and has anti-inflammatory activity of 22 units per gram (see Shapiro et al., J. Am. Pharm. Assoc., Sci. Ed., 46, 333 (1957), for reference as to method of testing).

The novel compound of this invention can be combined with solid or liquid pharmaceutical carriers and formulated into the form of tablets, powder packets or capsules, or dissolved in suitable solvents for oral and parenteral administration for human or veterinary use.

It is to be understood that it is intended to cover all changes and modifications of the examples herein chosen for the purpose of illustration which do not constitute departures from the spirit and scope of the invention.

We claim:

The compound CONHCH|C ONHCHr C5 Gonnmo cnrcnnoc N No references cited. 

